32953-62-1Relevant articles and documents
Stereoselective synthesis of new glycooxathiecinone using vic-cyclic thionocarbonate haloalkylation and ring closing metathesis as key steps
Benazza, Mohammed,Kanso, Rami,Demailly, Gilles
, p. 8885 - 8890 (2009)
Herein, we describe the first glycoconjugate macrocyclic thiolcarbonate namely (Z)-10(S)-[3′-O-acetyl-1′,2′-O-isopropylidene-4′-deoxy-d-erythrofuranose]-4,7,9-trihydro-10H-8-thia-1,3-oxathiecin-2-one (17a) using a strategy based on two key steps synthesis: (i) a haloalkylation of vic-diol via their cyclic thionocarbonate derivatives; (ii) a macrocyclisation using ring closing metathesis reaction. Detailed here is a newly developed extension of vic-diol halogenation via the cyclic thionocarbonate function but using a range of alkyl halides other than the customarily used MeI. For example, with 1,2-O-isopropylidene-5,6-O-thionocarbonate-d-glucose (1) and allyl bromide, the 5-allylthiolcarbonate-6-bromo-6-deoxy-d-glucose derivative 6 was obtained in good yield. The later submitted to 6-allythioetherification and ring closing metathesis (RCM) with Grubbs second generation gave stereoselectively the target oxathiecinone 17a in 75% yield for the RCM step.
TRIALKYLTIN RADICAL USED TO CATALYZE THE O,S-REARRANGEMENT OF CYCLIC THIONOCARBONATES. A NEW ENTRY TO THIO-SUGARS
Tsuda, Yoshisuke,Kanemitsu, Kimihiro,Kakimoto, Kyoko,Kikuchi, Tohru
, p. 2148 - 2150 (2007/10/02)
The cyclic thionocarbonates give O,S-rearrangement products, the thiolcabonates, in appreciable yields, when treated with a catalytic amount of tributyltin hydride and α,α-azobisisobutyronitrile.This reaction opens a new route to regioselective preparatio